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Check availability on Chestertown Gay-Friendly Hotels

Our top choices for Chestertown LGBT-friendly hotels

Private beach nearby, sun-loungers, beach volleyball

The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.5 star property
Chestertown
7.8 out of 10, Good, (77 reviews)
"Very nice rooms, "
United States
Stephania
The price is ₹9,957
₹11,384 total
includes taxes & fees
17 Mar - 18 Mar
The Lodge at Great Oak Landing
Lobby lounge

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (429 reviews)
"Arrived earlier than expected and the staff was very accommodating and friendly which made for an excellent stay from start to finish. "
United States
Linette
The price is ₹6,554
₹7,275 total
includes taxes & fees
24 Mar - 25 Mar
Red Roof Inn & Suites Chestertown
Free daily full breakfast

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (885 reviews)
"Staying is peaceful and the rooms clean."
United States
Robert
The price is ₹9,635
₹10,695 total
includes taxes & fees
19 Mar - 20 Mar
Comfort Inn & Suites Chestertown
Lobby lounge

Flag House Inn

Flag House Inn
3.5 star property
Historic District
9.4 out of 10, Exceptional, (87 reviews)
"The Inn is beautiful and the staff very welcoming. My room was spotless, cozy, and tastefully decorated. The location is directly across the street from the USNA. I skipped breakfast, but the offerings looked lovely. Will definitely stay here again. "
United States
Elizabeth
The price is ₹16,099
₹18,353 total
includes taxes & fees
16 Mar - 17 Mar
Flag House Inn
Exterior

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
2.5 star property
Grasonville
9.2 out of 10, Wonderful, (972 reviews)
"Check-in was great! The young man at the desk was so friendly and helpful!! Room was clean and beds were clean and comfortable!"
United States
Kelley
The price is ₹9,957
₹11,052 total
includes taxes & fees
23 Mar - 24 Mar
Holiday Inn Express Annapolis East-Kent Island by IHG
Exterior detail

Vandiver Inn

Vandiver Inn
3.5 star property
Havre De Grace
9.4 out of 10, Exceptional, (536 reviews)
"a wonderful place to stay with super friendly staff. easy walks to downtown and restaurants. stayed here before and definitely will be back"
United States
Dieter
Vandiver Inn
Terrace/patio

Home2 Suites by Hilton Baltimore / Aberdeen, MD

Home2 Suites by Hilton Baltimore / Aberdeen, MD
3.0 star property
Aberdeen
8.8 out of 10, Excellent, (353 reviews)
"Awesome staff, very clean, great pool Awesome breakfast!!! All good things"
United States
Patty
The price is ₹9,022
₹10,105 total
includes taxes & fees
22 Mar - 23 Mar
Home2 Suites by Hilton Baltimore / Aberdeen, MD
Terrace/patio

Fairfield Inn & Suites by Marriott Aberdeen

Fairfield Inn & Suites by Marriott Aberdeen
3.0 star property
Aberdeen
9.0 out of 10, Wonderful, (317 reviews)
"Clean rooms"
United States
Eric
The price is ₹10,094
₹11,305 total
includes taxes & fees
29 Mar - 30 Mar
Fairfield Inn & Suites by Marriott Aberdeen
Terrace/patio

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1,002 reviews)
"Staff was friendly and rooms were clean. Beautiful area to visit. "
United States
Amy
The price is ₹10,509
₹11,664 total
includes taxes & fees
18 Mar - 19 Mar
Hilton Garden Inn Kent Island Marina
Lobby

Homewood Suites by Hilton Bel Air

Homewood Suites by Hilton Bel Air
3.0 star property
Bel Air
8.8 out of 10, Excellent, (476 reviews)
"Nice accommodation"
United States
Cecilia
The price is ₹8,997
₹10,076 total
includes taxes & fees
30 Mar - 31 Mar
Homewood Suites by Hilton Bel Air
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chestertown Hotel Reviews

Frequently asked questions

Searching for an LGBTQ-friendly hotel in Chestertown?
Whether you are travelling with your partner or flying solo, you'll find Chestertown hotels that are members of the International Gay & Lesbian Travel Association on Expedia. Discover the people, places and traditions found only in Chestertown.
What is the top LGBTQ-friendly place to stay in Chestertown?
Comfort Inn & Suites Chestertown is a top LGBTQ-friendly hotel, and features free breakfast and free WiFi. Red Roof Inn & Suites Chestertown and The Lodge at Great Oak Landing are other good options for your stay.
How many LGBTQ-friendly hotels will I find in Chestertown?
There are currently 3 LGBTQ-friendly hotels in Chestertown.
What should I do while I'm visiting Chestertown?
During your trip, get out and enjoy everything Chestertown has to offer. You and your travelling companions may want to visit Historical Society of Kent County Maryland, Northern Chesapeake Bay and Chesapeake Bay. While you're here, create some great memories of your trip with stops at Garfield Center for the Arts at the Prince Theater, Chestertown Historic District and Rolphs Wharf Marina.
What is a gay-friendly hotel in Chestertown?
LGBTQ-friendly hotels are places where lesbian, gay, bisexual and transgender travellers are proudly welcomed. Expedia has worked with the International Gay and Lesbian Travel Association (IGLTA) to compile a selection of LGBTQ-friendly hotels worldwide. In Chestertown, hotels affiliated with IGLTA prioritise a diverse environment in which guests are welcomed, respected and not obliged to declare or hide their sexual orientation.
What can I expect from LGBTQ-friendly accommodation in Chestertown?
Take a holiday from the ordinary; stay at a gay-friendly hotel in Chestertown, and the staff will help you explore the local gay scene and the LGBTQ+ culture. Many of our LGBTQ-friendly accommodation options offer community-specific packages, exclusive tours and opportunities for social interaction.

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